Osceola has hosted such artists as Lindsey Stirling, Echosmith, Kiiara, Velvet Revolver, Lynyrd Skynyrd, Clay Aiken, 9th Wonder, Pentatonix, Peter Cottontale, Marcus Anderson, Blues Traveler, Obie Trice, Gnarls Barkley, Jason Michael Carol, Cash Money, Hootie and The Blowfish, Cravin’ Melon, Corrosion Of Conformity, Confessor, Flat Duo Jets, The Accelerators, Donna The Buffalo, Clay Walker, Roomful of Blues, Erykah Badu, Troop 41, Big Daddy Kane, Michael Gillespie, J. Cole, Bas, Yo Gotti, Marc Law, 

and many, many more...